


Deadlocked Deal

by Lady_Nightshade30



Series: The Cowboy's Lawyer [1]
Category: Overwatch (Video Game)
Genre: Deadlock Jesse, F/M, First Meetings, Flirting, Intern Ashton, Jesse turns, Language, Pre-fall Overwatch, deal making
Language: English
Status: Completed
Published: 2018-09-17
Updated: 2018-09-17
Packaged: 2019-07-13 10:04:52
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,820
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16015655
Author URL: https://archiveofourown.org/users/Lady_Nightshade30/pseuds/Lady_Nightshade30
Summary: When Ashton Prentice interns at her aunt's law office in the Overwatch buildings she accompanies the older woman to deal with the paperwork when Blackwatch takes down the dangeorus Deadlock gang, there she meets the man who despite his young age is still high up on the leader ladder. She attraction is immediately and Reyes decides to use honey as opposed to vinegar to get Jesse to sign up for Blackwatch.





	Deadlocked Deal

**Author's Note:**

> This is the first part of the Jesse/Ashton series. A huge thanks to LittleScrib and insaniaTorn who helped me work through certain plot holes and did some betaing for this.

Ashton huffed a stray lock of brown hair from her face as she hurried down the hallway of the Blackwatch Headquarters in New Mexico behind her Aunt Maggie. The cold tiles of the floor soaked through Ashton’s silk stockings, helping to soothe her aching feet as she clutched a large file and her ruined pumps against her chest while a briefcase dangled from her other hand. She had removed the shoes because the heel had broken off one of them after she had taken a misstep on the stairs outside the building, something that annoyed her greatly because they weren’t even a year old and they had been a gift from one of her cousin’s when she turned sixteen earlier this year. Commander Reyes had called her aunt’s legal team because he and his group of operatives had just taken down some of the main strongholds of the Deadlock gang as well as some of the top members of the gang in the area. And the intimidating leader of Blackwatch thought one of the key members would do good in his special ops unit with his impressive skills. So Ashton’s aunt had to bring all the paperwork that would be needed for the transfer should he agree to join or declined. One stack was to clear his records, give him a clean slate as well as the usual paperwork to get him signed on and other one was too send him away for the rest of his life if he didn’t agree to join Blackwatch. The folder Ashton held was filled with papers and information that might help them figure out how to help tip the scales into Reyes’s favor.

“Agent Fairchild,” Maggie said as she approached the red headed male guarding the interrogation room door. “Is Commander Reyes available?”

“He’s in with the Deadlock brat he wants to hire at the moment, let me get his attention real fast.” The male answered around the toothpick in his mouth, shrugging his shoulders while pulling away from the door a bit before reaching up and tapping on the door behind him with his knuckles. 

A couple minutes later when Commander Reyes opened the door to step outside Ashton heard a snarling smoother Southern voice cussing at the commander’s back, which caused the commander to snap back at the owner about watching his mouth. Just when it looked like the male teen was about to continue his shouting his eyes locked on her and she was given a clear view of his dark amber eyes, well eye considering one was swollen shut from bruising, that belonged to a semi muscular boy about her age in a black, skin tight shirt as he released a low whistle of appreciation at the sight of her. He was tan with rich, mahogany hair to go with his dark eyes. A trickle of blood was trailing down his strong, clean shaven chin from a busted up lip that was currently curled up into a charming smile in her direction. He raised a hand in her direction in a small wave, despite the handcuffs keeping him secured to the table as he attempted to look relaxed and charming despite the obvious beating he had taken and probably not having much room to move with the cuffs attached to the table. The affect is somewhat ruined by the blood dripping from his nose, past the toilet paper that was stuffed up there. Still though, she considers has she stares at him, he is kinda cute. 

“Well hello Darlin.” he practically purred.

 

Gabriel Reyes scowled in irritation at the youth, Jesse McCree, sitting across from him at the table in the interrogation room. The smartass had been giving him lip ever since he brought him in and hadn’t shut up about wanting his goddamn hat back. He was starting to seriously reconsider his offer because he didn't think he could put up with the kid’s mouth no matter how talented he was at shooting and fighting and based on the little shit’s smug expression he knew it, which is probably why the kid was doing whatever he could to push Reyes’s buttons, when there was a slight knock on the door.

“You’re in luck kid,” Reyes said as he got to his feet and pulled himself to his full height. “Looks like you’ll get a chance to think over my generous offer while I handle somethings in the hall.”

“Doubtful you old bastard,” the boy snorted. 

“You should seriously consider my offer,” Reyes said as he placed his hand on the knob. “Better pay, better benefits, and we’ll actually have your back; unlike those fuckers who only claim to have it.”

That said Reyes opened the door preparing to greet Maggie Hardison and her niece, Ashton, who was interning for her aunt in the law offices of Overwatch over the summer. 

“Eh fuck you, you fucking-.” Jesse snarled at his back, his tone rising to be heard over Gabriel as the older man shouted at him to watch his fucking mouth. The chaos ceased when the kid caught sight of the young girl and let out a wolf whistle before he drawled out. “Well hello Darlin.”

Gabriel stopped as he took a minute to look back and forth between the two teens, an idea forming in his mind as he turned to face the two women letting the door close behind him. 

Maggie narrowed amber eyes at him from beneath her long ashes and flared her small nose, dark.cheeks flushing red in anger when she realized he was staring thoughtfully at her niece. 

“Don’t even think about it Commander.” She said sternly.

Reyes sighed. “Look she’s the first thing he’s shown interest in aside from being a complete and total pain in the ass. Not to mention bitching about his damn hat.”

“I do not see what that has to do with Ash.”

“He might be more willing to sign on with us if he thinks he’ll get the chance to talk to her on a regular basis.”

“So your plan is what?” Ashton asked curiously in her smooth English accent as she stared at the Blackwatch commander. “Tell him, ‘join us and you might get laid without having to pay for it’?”

“Pretty much yeah.” Reyes said turning to look at her. 

“Forget it,” Maggie interrupted moving to stand between them and stare down the commander as best she could despite the height difference. “Don't you have someone on staff close to his age you can use? My niece doesn't have the training to interrogate someone.”

“On missions or in the med bay. Anyways she won't be interrogating him, she’ll be talking to him. See if she can't get anything out of him that we can use to our advantage to turn him. Besides he’s chained up by his wrists and ankles so there is no way he will be able to escape and hurt her. Even if he does-.”

“What do you mean, ‘even if he does’?” her aunt demanded. 

Reyes sighed in irritation as he ran a hand over his shaved head aware of the way Ashton was eyeing the door from time to time in contemplation during the argument. “Look, there will be three agents, plus me, in the observation room, not to mention Agent Fairchild just outside the door. We’ll stop him before he manages to even lay a hand on her, your niece is going to be fine.”

Ashton watched her aunt and the commander go back and forth for a bit, both faces twisted tight into stubborn lines refusing to budge, before glancing at the door to the interrogation room. Fairchild caught her eye and motioned to door while placing a hand on the knob, an eyebrow raised in question. She glanced back and forth between the arguing adults, swallowed her pride, and slipped in the direction of the cracked door. She shuffled somethings around a bit in order to grab the book and cowboy hat the Special Ops agent held out to her before slipping through the door.

The sound of the door shutting caused the chained up teen to glance up, the angry scowl on his face changing to flirtatious in the blink of an eye along with his posture, which went from an annoyed slouched to a relaxed and at ease one. She felt the corner of her lip twitch at the sight. 

“Good afternoon.” She greeted as the door closed with a soft click behind her.

“Hello again Darlin,” he practically purred at her as she took a seat across from him at the table causing her face to heat up in embarrassment at both the tone of voice and the way he was looking her over. “Well now aren’t you just the prettiest little thing I’ve ever seen.”

 

Jesse glanced up when the door opened expecting to see the large fucker that had taken him and his friends down. But instead he saw the pretty girl who had been in the hallway when the big fucker had left a few minutes ago. He felt a smile spread across his lips and the action caused the split in his lower lip to open up again, spilling more blood down his chin, causing him to curse up a storm as he ducked his chin to dab at the blood a bit. He looked up at the pale brunette, who was definitely a vast improvement in his eyes to the bulky bastard that had been in here earlier, from under his eyelashes as he tried to stop the bleeding. His eyes trailed over her form taking in the black pants suit, that looked like it cost more than the monthly payments on his motorcycle, and the well kept, manicured fingernails. Despite the professional appearance her dark hair was swept into a simple braid that rested on her right shoulder, contrasting with the cream top. She held a briefcase and heels in one hand while the other clutched a file against her chest while his damn hat dangled from her fingers. Everything about her screamed money and innocence. He also knew damn well that she had been sent in to make him corporate with them, so she was probably smarter then she looked. But while he greeted her he knew that he had no intention of doing so he saw nothing wrong with stringing the bastards on the other side of the mirror along so he could have fun and spend as much time as possible with the pretty thing before him. He felt his grin widden at the sight of her blush because he damn well knew he looked good, even if he was banged up to all hell. He had managed to seduce more than his fair share of information from the wives, girlfriends, and mistresses of various other gang leaders on behalf of the Deadlocks to know what he was doing when it came to seducing the opposite sex. No matter how many bruises, scars, or wounds he was sporting at the time; hell some of the women even wanted him because of them.

No matter what some women just wanted a bad boy and few were badder than a top ranking member of a large gang, no matter how young. And in his experience the richer they were, the younger they were the badder they liked their boys. He wandered vaguely how bad she liked them. 

Well, he decided licking his lips as she crossed the room, there was only one way to find out.

“What’s the matter Sugar?” he asked. “Cat got your tongue?”

“Not at all,” she said smiling at him as she placed the file with his information on the table and her briefcase beside her on the floor along with her shoes. “Mr. McCree is it?”  
Jesse locked his thumb and cleaned away the dried blood that was left over now that he had stopped bleeding. “Oh come now Darlin you don't have to call me that. You can just call me Jesse.”

“Very well,” she said we she pushed the well worn novel towards him as a peace offering. “Jesse then.”

“As thankful as I am to you returning my book,” he started reaching for and flipping through the pages nonchalantly. “I can't help but wonder what the chances are of you giving me back my hat.”

“Well I’ll tell you what Jesse,” Ashton said as she opened his files and started flipping through them curiously. “If you play nice and behave yourself i’ll let you have it back but for now it is going to stay with me.”

The male brunette grinned at her, “Wear my hat for me and I’ll play as nice as you want Sugar. Unless you're afraid I'll give you lice or fleas.”

Ashton glanced up at him, seeing the challenge in his eyes and glanced briefly at the dark brown cowboy hat before looking back at him. She reached for the hat with one hand, never once taking her eyes off him as she placed it on her head. 

“Of course not,” she said cheerfully as she settled more comfortably into her chair and crossed her legs. “Otherwise you would smell like tar instead of tobacco.”  
Jesse let out an appreciative whistle at the sight of her. “Darlin had I known you would look this good in my hat I would have asked for you sooner.”

“You’ve never met me before,” she teased. “So how would you have known to ask for me?”

“Easy Sweetheart,” Jesse said smoothly. “You’re exactly my type and I would have asked to speak with someone who would have given me one hell of a view. Or at least a better view than the old man who was in here earlier.”

“Even if you had no intention of signing on?”

“A man’s gotta have his principles doesn’t he?” Jesse smirked before cursing loudly when the cut on his lip split open again causing blood to flow down his chin.

“Yes I suppose he does,” Ashton said while trying not to laugh as she handed him one of her handkerchiefs to stop the bleeding. “Here this might be more useful at stopping the bleeding then the tissue paper.” 

“Thanks Doll,” Jesse said as he accepted the square piece of cloth from her. 

Ashton flushed when their hands touched, earning her a smirk from the male across from her as he took the white, lacy piece of fabric, before glancing back down at the file in her hands. “It says here you got top marks in your school. Even after joining Deadlock you still managed to keep them up and your teachers were rather proud of you, aside from the whole joining a gang thing of course.”

“Of course.” Jesse said a little tightly, his shoulders tense. “What’s your point Darlin?”

“Why keep your grades up after you joined a gang if you didn’t plan on doing something else? I mean with these high marks you could have gone on to some of the top universities with full rides.”

“So?” Jesse asked trying to keep his charming smile on his face but she could tell by his eye that he was not happy about the direction this conversation was taking. 

“Why would you risk a promising future for the possibility of jail?” She asked as she held up the sheet that showed his grades while leaning forward slightly. “And loosing any possible scholarships? Why not just let your grades slip?”

“I’m sure my history is already in there,” Jesse said with a scoff. “So why ya askin me when you can just read it for yourself?”

“Because I would like for you to tell me.” Ashton answered gently.

“Why?” 

“I like the sound of your voice,” she said sweetly. 

“Fine,” Jesse said with a casual shrug. “My pops ran out on us when I was fourteen so I had to help mom keep food on the table and a roof over our heads. Since I was so young it was hard for me to get a job that was legal. Deadlock offered me a steady job and fairly decent paycheck to help with the bills. Plus they didn’t take taxes out, nor did they ask any unwanted questions.”

“How generous of them.”

Jesse smirked. “Well there were the benefits.”

“I hope those benefits came with good health insurance.”

Jesse’s smirk faded and his dark eyes flashed dangerously causing Ashton to pause briefly before pressing forward to remove the paper with the information on his mother’s hospital information which she presented to him. 

Ashton took a deep breath, wishing she didn’t have to hit this below the belt. “But it’s still not enough to help with this.” 

“What are you doing with my mother’s medical records?” Jesse asked tightly.

“Overwatch makes it our business to know everything about everyone it wants to join the organization.” She replied softly.

“No matter how hard you try to hide it.”

Jesse shrugged his shoulders in an attempt to look nonchalant. “Hospital records are easy for government agencies to get a hold of.”

“Perhaps,” Ashton agreed. “But how many know you were the one that saved the little girl from her abusive father and indifferent mother? Not even your fellow Locks know about that do they?”

“No.”

“Blackwatch is prepared to cover the remaining medical bills of your mother as well as move her into one of its private hospitals were she will get the best medical care possible.”

“What’s the catch?” Jesse asked narrowing his eyes suspiciously.

“A simple matter. Give us everything you know on the Locks and become a member of Blackwatch. And you get a clean slate.”

“Is that all?” Jesse asked curiously.

“Well you will get a steady paycheck, benefits, housing.”

“How often will I see you Sugar?” 

“Chances are Mr. McCree-.”

“I told you Darlin it’s Jesse.”

“Jesse.” Ashton said has she tried not to roll her eyes while fighting back a smile. “Since I will probably go into legal you will probably only see me unless its for legal matters like you overstepped your bounds in regards to the law or you have to give a statement in court, that sort of thing.”

“I guess if I sign up for Blackwatch I’ll just have to get in trouble with the law a lot.”

Ashton sighed and sat back crossing her arms but the corner of her lip twisted up a bit. “That won’t help you accomplish anything with me.”

“Oh come on Sugar don’t be like that,” Jesse said brushing the toe of his boot up against her foot. 

Ashton jumped and pulled her foot away tucking it beneath the chair as her lips twitched upwards. “Now Jesse, you said you’d behave yourself.”

Something is tapping at the back of her mind, something about how Jesse shouldn’t be able to reach her feet with his own. But she can’t bring it to the forefront of her mind no matter how hard she tries.

Jesse smirked at her as he placed his hands casually on the table and her eyes widened when she realized he was no longer shackled before standing up to his full height. “I may have lied about that just a little.”

Ashton swallowed down her fear and uncertainty before putting on her best poker face. “Sit down please.”

“Now why would I do that?” Jesse asked as he took his hat back and placed it on his head before burying his hand in her hair. “When I can play with you all I want now?”

“You can’t play with me all you want,” Ashton said. “I doubt you will have time to do much more after this. Besides you won’t hurt me.”

“What makes you say that?” Jesse asked as Fairchild and Reyes burst into the room pointing their guns at the younger man, who didn’t seem the least bit bothered by their presence or their weapons, followed closely by Maggie who was kept from the room by the sheer bulk of the two males. 

“Like I said you saved that one girl from an abusive father. But that’s not the only one you saved from an abusive household without the Locks knowing. You seem to have a thing against abusive father. Besides if you were free for as long as I suspect you were you would have already hurt me if you wanted to do so. So please sit down.”

“What are you going to do if I do play nice and join Blackwatch?”

“Go back to school and pass the bar.”

“Is that all?” Jesse asks getting in her face.

“Pretty much yeah. Now please just sit down.”

“What happens after you pass the bar? You going to join Overwatch as well?”

“Maybe.”

“So if I join Blackwatch I might get the chance to see more of you?”

“No promises.” Ashton said. “But I can guarantee that you have a better chance of seeing me again if you join then if you don’t.”

“And what’s going to happen if I don’t sign up for Blackwatch?”

“You will go into a maximum security prison for the rest of your life and you’ll never see me again.”

“So harsh Darlin.” Jesse chuckled as he took a seat and placed his feet on the table.

“So fact Darlin.” Ashton retorted. 

Jesse smirked. “Lets see the paperwork.”

Reyes and Fairchild looked at each other before slowly putting away their guns.

“Did he really just sign on to Blackwatch solely for the possibility of being able to chase her tail?” Fairchild asked as they moved forward. 

“Don’t forget the chance to take care of his mother,” Reyes said with a smirk. “Gotta love teenage hormones.”

Reyes placed a hand on Ashton’s shoulders signaling for her to get up so he could take over. 

“Don’t be going too far now Darlin,” Jesse cooed as Maggie looked her niece over, checking to make sure she was alright. “I need something pretty to look instead of just these ugly   
fuckers. I’ll behave this time I promise.”

“Very well.” Ashton said as Reyes took a pack of crumbled up cigarettes from his pocket and tossed them onto the table before the teen. 

Jesse flashed her a smile before retrieving a smoke and lighting it up as Maggie pulled the required paperwork from the briefcase and with Reyes assistance started going over the forms he needed to sign in order to get his fresh start. The entire time he kept glancing back and forth between Ashton and the papers the adults were pushing in front of him. 

Ashton sighed deeply and wondered how long it would take before they ran into each other again. She honestly couldn’t wait to see him again.

 

Later that night she would return to the condo with her aunt and realize she never got her handkerchief back from the boy.


End file.
